Heart Break
by Ariana Jones
Summary: What happens when Jeanette is dared to ask Simon out to prom and he friend zones her? She wants revenge, but what happens when her heart gets broken... twice? rated T just to be safe
1. Chapter 1

I do not own any of the Bagdarsarian characters 

It was late Saturday afternoon. I was reading a book from the library on couch.  
"Jeanette!," Brittany yelled from upstairs  
"What? I am at a good part in the story!"  
"Can you one up here?"  
"Can't it wait until later?"  
"No get up here now!"  
Ugh fine. I carefully bookmarked my page and tucked the book onto the bookshelf. What could she possibly want? I trudged my way up the stairs and into our room. Brittany was on the floor with her phone in the middle and Eleanor was across from her. I sat down and looked at her expectantly, wondering why again she called me up here.  
"I just downloaded a new game and wanted to play it with you guys," she said  
I mentally groaned on the inside. Whenever she did this it usually meant something bad that would last for a couple of hours.  
"Anyways it is a dare app that gives you dares when you press the button. You see I already put our names in it and chose a category." she smiled brightly.  
"Ohh so what category did you pick?" Eleanor asked  
"I thought we should start easy and do actions" with that she pressed the button and the game began.  
I have to say at first it was boring, but as the day went on the dares became more intense and I began to enjoy playing it. Eventually Brittany picked boys. "Your turn Jeanette"

" Do I really have to? I just went"

"yes" they both said simultaneously . Ugh I pressed the button hoping it would just say give your crush a hug or something along those lines. I closed my eyes, after the app beeped, symbolizing that it chose something. I heard my sisters giggling and talking . Uh oh, that's not good. I quickly read the phone, as I did I felt my face get pale. It said I had to ask out somebody of the other players choosing. I swore silently to myself, why did I have to get this one? "Alright Jeanette, Brittany and I have chosen the person and since prom is coming up you have it easy. You will be asking ...Simon!" " What! Why? You guys know I could never do that, besides we are just friends, if I take him to prom it would be weird!"

"Well its quite obvious that he likes you jean."

"really?" I said, my hopes raising slightly. Ever since we met the chipmunks Simon and I have been very close friends. Only a couple of years ago did I realize that I had feelings for him. But since I assumed he did not feel mutual I pushed those aside as not to distract me from our friendship  
"Oh definitely" Eleanor said with confidence.

"but there is a small catch," said Brittany with An evil smile. "you must...dramatic pause for effect... Ask him out in the next 30 minutes or if you chicken out we will do something to embarrass you." With that they grabbed me by my wrists and shoved me out the door. I turned around to try to get back into the house but to no avail. I knocked on the door. I heard Brittany say something about not letting me in until I get a date from Simon. I sighed knowing that she would keep the door locked until then. I looked down at my watch, it was 7:30. I took off down the street at a brisk pace. After a minute or so I arrived at the house I knew so well. The place where I had spent a few years of my childhood before Mrs. Miller adopted my sisters and I, the place where I go to get away from noise and just talk with my best friend. I sighed remembering all the good memories I have here. By that time I had walked up to the door and subconsciously rang the doorbell. The noise of footsteps coming closer to the door pulled me out of daydreaming. As I was pulled back to earth I realized what I had to do. I gulped. What was I going to say? "hi Simon, I was dared to ask you out to prom . Do you want to go with me?" I would sound so stupid! I wish it was as easy as that but knowing me, I would mess it up somehow. I know! I would go for subtle, just casually ask him. Ohh I was so nervous though. I don't want to be rejected!  
My train of thought crashed into tiny pieces when saw who opened the door. "Hi Jeanette" he said smoothly. He was wearing his trademark blue sweater with his black glasses slightly askew on his face. "Oh… hi Simon"  
"Please come in. Would you like anything to drink?"  
"No thank you, but thanks for asking" With that he lead me over to the living room and sat down. "So why did you come over here?" he said looking me directly in the eye. His steel blue eyes were so so dreamy. I could just look at them for hours. Snap out if Jean, remember why you are here?  
"I uh wanted to ask you s-something" Great I was so nervous that I was stuttering. I looked down at my paws and realized that they were sweating.  
"And what would that be?" he said.  
" I was uh w-wondering if maybe you wanted to do somethingwithmenextweek" I said in a rush.  
"I'm sorry I couldn't understand the last part could you please repeat that jean?"  
"I w-was wondering if you w-waned to do something with m-me next weekend. " I look up at him hopefully, praying that he understood what I meant.  
"I am so sorry but I already have plans to work in the lab the whole weekend. Besides we already see each other often with our study-session and practice with our siblings. Our friendship couldn't get any stronger" that was all I could take. He just thought of me as a friend nothing more. My sisters were wrong he... He didn't like me. I began to frown.  
"What is it jean? Was it something I said?" After saying my nickname so calmly something inside of me snapped. "God Simon do you realize what's next weekend!" I yelled. He looked at me with confusion in his eyes. "There have been signs up for it since last month!" he still didn't get it.

"It's PROM!" I just asked you to prom! And with that, I lost it. Tears began to stream down my face blurring my vision. "Oh jean, I am so sorry I didn't realize that! I thought you were just asking me as a friend to do something ."

"Sorry doesn't cut. Not this time Simon. I really thought you liked me, but I guess not. My sisters were wrong." With that I ran out of the house. I heard him calling my name telling me to come back but I just ignored him. Each time he said my name sent a stab to my heart, he just thinks of me as a friend, nothing more. How stupid was I! I actually thought I and a chance, but that's right, the great Simon Seville has to study before girls.

**A/N**

**This is my first story that I have published online. I hope you guys enjoyed it! :) Please review! **

**~A.J.**


	2. Chapter 2

I had to get away. In most cases I just go home when I became upset, but I didn't want people to talk to me at the moment. I made my way to my place of comfort, the library. As I entered the doors I saw Simon's favorite book shelf. I felt my body shudder at the thought of him, new tears crept into my eyes.

I ran. I needed a place that nobody would think to look for me, a place where Simon never visits. Without me knowing it I found myself behind the bleachers of the school's football field. I crawled into the darkest corner and cried until I couldn't. "_He doesn't like me_" was the only thought that went through my head. I felt my phone vibrate in my pocket like crazy, but I ignored it. It was unusual for me to be out this late and not answer my phone. In a little while my family would be looking for me, but I didn't care. I'd rather stay here for the rest of the night than face my family and him.

While I sat in myself pity I felt my swollen eyelids become heavy. Before I knew it had dosed off. When I woke up it was pitch dark. I checked my phone to see the time. 10:54. My eyes nearly popped out of my head. Everyone must have been looking for me! I began to crawl out to head home, knowing I would have to face everybody sooner than later and be in huge trouble with Ms. Miller for being out so late.

I heard a branch crack and a person talking. I swore silently to myself. Why had I stayed out this long? Who knows what happens at this time of night, I was so stupid! As the person came closer I pushed myself closer to the wall. But wait, that voice seemed familiar.

"Yeah Dave, I'll be home soon. I am still helping to find Jean. Yes, I'll be careful. Yeah, Yeah I will be back by 12. Okay see you soon. Bye"

It was Alvin. I let out a sigh of relief.

"Who's there?" Alvin asked.

I crawled out of my hiding place. "It's me."

"Jean! Oh thank god! We have been looking for what seems like forever. Everyone is so worried!" He came over to me and gave me a hug. I had never seen him like this before. It was weird, but nice to see the sweet side of him.

"But seriously, what the hell were you thinking? We were going to call the police if we didn't find you." And then he was back.

"Look Alvin, I'm sorry okay," I said, "I just needed some alone time"

"So what was so BIG that caused you to go missing for 3 hours?"

"It's a long story that I don't want to talk about."

"Come on Jean, we have time." and with that he lead me to the bleachers and sat down next to me. I sat there looking at him as if he were crazy. Since when did the "macho" Alvin Seville care about anyone other than himself?

He looked at me expectantly. I sighed and gave in. In no time at all I had told him the events of the evening. He sat there and listened intently and gave me sympathetic glances. By that time I had finished I started to cry again. It hurt so much to talk about it, to let the truth seep in. But the most unexpected thing happened. He pulled me into a hug and comforted me.

"Sush Jeanette…..It's okay. Simon is really smart and all, but he is completely clueless when it comes to girls." I just nodded in to his sweatshirt in response. "hey, if it makes you feel better we can get back at him?"

"That would … be ….nice" I said in-between sniffles.

"Okay, I'll set something up. Come on now, we better get you home now." With that he stood up an offered me a hand. We started to walk back to my house. I actually began to feel better, I knew it was bad to hurt people, but hey, he deserved it. For the first time since my encounter with Simon, I found myself smiling.


	3. Chapter 3

After Alvin had dropped me off at home, I slipped into my room to avoid questioning from my sisters. I quickly put on pajamas and hopped into bed. No sooner had I put the cover over my head did my door open.

"See I told you she didn't want to talk Brit, just let her be by herself for a while," Said Eleanor in a hushed tone. Brittany sighed but shut the door.

I awoke in the morning at about six, like I usually did. I sighed and stood up knowing form experience that I wouldn't be able to fall back asleep. I made my bed quickly and tidied up my room. My mind kept wondering back to the events that happened yesterday. I needed to get up and go somewhere to get my mind off of it. I got dressed and headed downstairs. I didn't want to worry everyone again, so I left a note on the refrigerator, grabbed my phone and keys, and then walked out the door.

I needed to do something different, something dangerous. I felt changed, liked part of me disappeared yesterday. I needed to do something that would make Simon cringe at the thought. I got it! I flipped open my phone and texted a friend asking for a favor.

* * *

About five minutes later I arrived at the house where my heart shattered. As I walked up the driveway the garage opened. Standing there was very tired looking Alvin. "God Jeanette, how do you get up so early?"

"It's an old habit, so can I borrow it for a while?" I asked almost pleadingly. "I'm not sure… I mean why do you even want to do this again?"

"Come on Alvin, I thought you were the fun one! Besides it would make your brother angry. You know you want revenge just as much as I do" I said slyly.

"Fine, just promise not to scratch her okay?"

"Jeez, you treat it like it is alive," gave him a playful shove. "I promise not to scratch it okay, now come on give me the keys!"

He gave me one last look over than dropped the keys reluctantly in my hand. "You know I am doing this because you are the responsible ones out of your siblings right? I mean if Britt were to ask me I would totally refuse her."

"Yeah I know," with that he lead me over to the corner of the garage where something was covered with a brown cloth. I couldn't wait any more; I yanked the cloth off to reveal a motorcycle.

It was a crimson red; it looked as if it was brand new. I giggled with excitement. I knew that Alvin had bought it used a few years ago and repaired it by himself. Boy! did his work pay off! We stood there for a minute just admiring the handy work. I heard him clear his throat. "So remember to not scratch her up and get back here before dark, got it?"

"Yes, dad," I said with a laugh. With that I hopped on the bike and revved the engine. He handed me a helmet and gave a thumbs up with a smirk. I laughed and took off down the street. I looked behind me once to see Alvin laughing and shaking his head.

* * *

To be honest I was scared out of my mind for the first few minutes of the ride. I was supposed to be the responsible one! What was I doing riding a motorcycle at seven in the morning? Oh well screw it! I was already going and adrenaline I felt running through my veins was exhilarating. Before I knew it I had steered myself to the highway that lead to the beach. I parked the bike and walked down by the shore. It was so peaceful here, the waves lapping at the shore the sun hitting my face. I could just see Simon's face burning with anger and worry. It made me laugh out loud! If it weren't for him, I would still be at home this morning probably curled up on the couch reading a romance novel.

I spent the rest of the day there and actually went into the water. It was cold, but fun. By the time I started heading home it was about 5. All my feelings melted away into a wonderful bliss like feeling. I truly didn't want to go, but knew I had to. I started up the bike and made the 30 minute drive back home.

As I pulled into the drive way I saw the boys playing catch. I saw Theo's eyes cloud with confusion as why I was driving a motorcycle. Simon's face had no emotions, but you could see in his eyes the look of shock and disappointment in them. I smiled at my small victory of making him upset. By that time Alvin had run up to me to help with the bike.

" So what do you think?" he asked

"It purrs like a kitten" I said with a smile.

"Good, I see you didn't wreck her. I was so worried all day, I mean you are clumsy" I punched his arm playfully.

"Alvin, just because I trip over my tow feet doesn't mean I'm incapable of driving a motorcycle"

"Well I'm just glad you enjoyed yourself. If you want to ride her again just call me okay? Also when you get up tomorrow for school, make sure you look your best, I have a little surprise planned."

"Okay, I'll see later then!"

"Yep, bye Jean!" he called. I walked out the garage and waved good bye to Theodore. I heard Simon call out good-bye, but I ignored him.

When I arrived home I went over to the table to see if I had any mail, I did. I grabbed the latter and made my ways back upstairs. The house was quiet so I assumed that my sisters were out. I sat down on my bed and opened the letter. I squealed with delight.

I was accepted! You see, I had applied to a foreign exchange program a few months ago, just for the heck of it. It was really hard to get into, but I did it! Although it said that I had to be at the airport by Sunday morning because my flight left at 5 a.m. That was right after prom. Oh well.

I curled up on my bed rethinking the day's events and drifted off into a blissful slumber.

* * *

**A/N**

**So what did you guys think? Did you expect Jeanette to do that? (I know it is a little out of character) Rate and Review!**

**Fierce, Love, and Chipmunks,**

**~A.J.**


	4. Chapter 4

I awoke in the morning to a bright light shining on my face and someone standing over me.

"Just five more minutes," I mumbled.

"No, you get up now, I have a lot of work to do on you," said Brittany. I sighed and sat up in bed rubbing my eyes.

"Now you go take a shower while I find clothes for you," she said while shoving me towards the bathroom. I went in and took a shower half asleep. As I was getting out I hit my shin on the edge of the bathtub. I cursed my clumsiness as I hobbled out with a towel wrapped around me.

I found Brittany going through my closet mumbling stuff about "how this will never do". After a few minutes she walked out of the room for a few minutes. When she came back she had a bag from the mall and her make-up kit. She gave me the bag and told me to try the clothes on. I sighed and walked back into the bathroom. When I came out she blind folded me and told me to stay still. I felt her touching my face and hair and became worried. I don't usually let people do this kind of thing to me without me fighting back. But I guess this time I had a good reason. I was going to get revenge, plus Alvin said I had to look my best today for some reason.

After what felt like an hour she finally took off the blindfold. I put my glasses on and looked in the mirror. I gasped! I barely recognized myself staring back. I had on dark blue skinny jeans with a striped blue and white t- shirt that showed my stomach. My hair was down and was very nicely curled. I walked over to Brittany and gave her a hug.

"Thank you!," I said with a smile.

"No problem, anything to help my little sister out"

"I have just one question."

"Yes?"

"Where did you get the clothes, I mean none of your stuff would fit me."

"Let's just say I wanted to be prepared if something like this ever came up," and with that she walked out of my room.

I smiled, typical Brittany, always prepared to do a makeover. I glanced over at the clock. Jeez! I had to start walking if I wanted to be on time. I grabbed my bag and ran out the door.

By the time I had gotten to school, I felt weird about my new look. I mean sure I was used to people looking at me, but now everyone was looking. I unpacked my bag from my locker and stood up to see Alvin leaning next to me.

"Good, you listened to what I said"

"I had to, Britt woke me up and did this" I said while motioning to myself. He chuckled at my comment.

" Well, have fun day Jean" he said and walked away. I stood there with a confused look on my face. Alvin never talked to me at school, let alone wish me a good day. I shook my head to clear my thoughts, I only had a few minutes to get to clad. Sure I may look different, but I still have expectations to meet.

* * *

Before I knew it the school day was over. I walked back to my locker to see one of Alvin's foot ball buddies leaning near it. I frowned. Even though my look made me almost instantly popular, that didn't mean that football players just start talking to you. I opened my locker and started to pack away all my stuff.

"Hey gorgeous" said Ethan. I giggled and blushed a little. Nobody had ever called me that before.

"Hi," I said.

"So, I was wondering if a pretty lady like yourself wanted to be my date to prom?," he said smoothly. I bit my lip. So this is what Alvin meant, that's why I had to look so nice. I was about to say no when I glanced to my right and saw Simon staring at us. I stood up and smiled.

"Of course I would!" I said while hugging him. It was a little awkward saying yes to someone I didn't know.

"Great, see you later," he walked away with a wink. Out of the corner of my eye I saw Simon storm off down the hallway. I smiled a huge grin. If felt great to get revenge. I knew it was wrong, but hey why not enjoy while you can.

I was so excited. I actually had a date to prom. The nerd girl had a date. I practically skipped all the way home. After I finished my homework, I immediately went online and looked up all the different types of dresses. By the time I was done, it was one in the morning. I sighed and fell back onto my bed with a smile. I fell asleep with the day's events still swimming in my head.

* * *

**Thoughts? I hope you enjoyed! Rate and Review!**

**Fierce,Love and Chipmunks**

**~A.J.**


	5. Chapter 5

**A/N **

**I am SOOO sorry for not updating lately! I kept getting caught up in other things so I promised myself to update tonight. Anyways here is the next chapter! **

**Reviews:**

**(I'm going to reply to the reviews in the beginning of the story to try something new! So keep and eye out for yours!)**

**alvinandbrittany4ever: Yep, her sisters are indeed going to the Prom with Alvin and Theo. (regular pairings)**

**simonettefan: Thanks! You shall see their reactions soon. (Mwhahaha evil laugh) ;)**

**ChipettesRock00: Thanks! I appreciate the interest in the story.**

**Guest (sorry, I don't know who you are so I am going to to refer to you as guest): Yes, suck on that Simon! :)**

**simonettefan (again) : yep, the next chapter is going to be drama filled! **

* * *

The rest of the week went by smoothly. That is of course the mornings. Sure it was nice to have a new look but it was so tedious! It was the same thing every morning. I would get up shower then Brit would make me up. On Wednesday afternoon I took everything off and tried to recreate it myself so that way she didn't have to do it for me. I failed miserably. I had burns on my head; makeup was all over the counter and my hands. I looked like Frankenstein's bride with a bad hair day. To be honest my AP chemistry homework was easier then this!

But I guess doing this every morning was worth it. I mean my popularity status rose drastically and I wasn't teased anymore so there was one positive. Another was that people actually talked to me. Sure I am shy, but it is nice to have someone to chat with, although nobody got my science jokes.

So today was Friday, the day I was going to go dress shopping my sisters. I was originally going to go with them after I asked Simon, but that didn't exactly go to plan.

At the moment I am in the car listening to my sisters babble on about their dresses and dates. I silently curse them. Why did they get to have the guys they wanted? I mean Alvin and Theo look so cute with them. Sure, Ethan is nice, in his own jocky way. But Simon, he's nerdy like me and gets the bad jokes I make. I don't have to be my fake popular self around him.

Wait? What am I thinking?! He friend-zoned me! He didn't even have the guts to ask me to Prom, I had to ask him myself. I mean what guy doesn't know about Prom? My hands gripped the steering wheel tighter turning my knuckles white. The happy vibe in the car slowly turned to one on concern.

"Are you okay, Jean?" asked a very concerned Eleanor.

"Yeah, fine. I'm just caught up in my thoughts." I replied.

"Okay," she said unsure," you know if you want to talk about it we are always here."

"Uh-huh, can we just get a dress and go." I said as we pulled into the store's parking lot.

* * *

20 dresses and three hours later we finally found the perfect dress. I went up and paid for it, glad that the long shopping day was over. It was fun the first few dresses, but Brittany insisted that we find the perfect dress for me. I struggled and tried to leave at first, but she took my keys. After I paid, I walked outside and put the dress delicately in the back of the car.

The drive home was fun. We had the music blaring and were singing along, having a good time. We pulled into our house and got out. Brittany insisted that she would carry dress inside, saying how my clumsiness would do something to it. I sighed and agreed, knowing that she was somewhat right.

"Hey, Jean you have something here for you" called Brit. Huh- that's weird, I don't remember ordering anything. I went to the front door to see a bouquet of red roses with a card addressed to me. I gasped, No one, and I mean no has ever before gotten me flowers. I ran inside and put them in a vase. I carefully walked up the stairs and set them down on my dresser. I grabbed the card and read it.

Jeanette,

I am so glad you are my date to prom. You truly are a gorgeous girl! Can't wait for tomorrow night!

~Ethan

I squealed with delight and laid back on my bed. I spent the rest of the night re-reading the card and tracing the letters until I fell asleep.

* * *

**So what did you think? (I know it was pretty short, but I promise the next chapter will be longer!) Rate and Review awesome people!**

**Fierce, Love, and Chipmunks,**

**~A.j.**

**P.S. I was thinking about doing a sequel. So if you guys want that to happen make sure you review!**


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